DE81297C - - Google Patents
Info
- Publication number
- DE81297C DE81297C DENDAT81297D DE81297DA DE81297C DE 81297 C DE81297 C DE 81297C DE NDAT81297 D DENDAT81297 D DE NDAT81297D DE 81297D A DE81297D A DE 81297DA DE 81297 C DE81297 C DE 81297C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- solution
- cresotinic
- homohydroquinonecarboxylic
- melting point
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- WXTMDXOMEHJXQO-UHFFFAOYSA-N Gentisic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 claims description 4
- 229960005219 gentisic acid Drugs 0.000 claims description 4
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 150000007965 phenolic acids Chemical class 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- WHSXTWFYRGOBGO-UHFFFAOYSA-N 3-methylsalicylic acid Chemical compound CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 3
- NJESAXZANHETJV-UHFFFAOYSA-N 4-Methylsalicylic acid Chemical compound CC1=CC=C(C(O)=O)C(O)=C1 NJESAXZANHETJV-UHFFFAOYSA-N 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L Potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 239000004159 Potassium persulphate Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- MMAILVQCTYZSRT-UHFFFAOYSA-N benzene-1,4-diol;sulfuric acid Chemical compound OS(O)(=O)=O.OC1=CC=C(O)C=C1 MMAILVQCTYZSRT-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 230000000640 hydroxylating Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- -1 iodine potassium Chemical compound 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N oxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OQUKIQWCVTZJAF-UHFFFAOYSA-N phenol;sulfuric acid Chemical class OS(O)(=O)=O.OC1=CC=CC=C1 OQUKIQWCVTZJAF-UHFFFAOYSA-N 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
In der Patentschrift Nr. 81068 ist gezeigt, dafs, wenn man eine alkalische Phenollösung mit einer Persulfatlösung zusammenstehen läfst, Oxydation an der p-Stellung eintritt, und dafs sich hierbei ein eigenthümliches Zwischenproduct, nämlich Hydrochinonschwefelsäure, bildet. Weitere Versuche haben nun ergeben, dafs man vermittelst der Persulfate in wässeriger Lösung auch bei den Carboxylderivaten des Phenols mit freier p-Stellung eine Hydroxylirung bewirken kann, und dafs sich hierbei ebenfalls eigenartige Zwischenproducte bilden, die als Derivate der Phenolschwefelsäure aufzufassen sind, die aber beim Erwärmen mit Säure in die entsprechenden Oxyphenolderivate übergehen.In patent specification no. 81068 it is shown that if one uses an alkaline phenol solution can stand together with a persulfate solution, oxidation occurs at the p-position, and that a peculiar intermediate product, namely hydroquinone sulfuric acid, forms. Further experiments have now shown that the persulphates can be used in aqueous solutions Hydroxylation also occurs in the case of the carboxyl derivatives of phenol with a free p-position can cause, and that in this way also peculiar intermediate products are formed, which are to be understood as derivatives of phenol sulfuric acid, but which when heated with Acid pass into the corresponding oxyphenol derivatives.
Das Verfahren ist dasselbe, wie es in der oben erwähnten Patentschrift angegeben ist. Es wurden so erhalten:.The procedure is the same as indicated in the above-mentioned patent. It were obtained like this:
aus Salicylsäure: Hydrochinoncarbonsäurefrom salicylic acid: hydroquinonecarboxylic acid
(oh COOH O4h),(oh COOH O 4 h),
Schmelzp. 196 bis 197°,Melting point 196 to 197 °,
aus o-Kresotinsäure: Homohydrochinoncarbonsäure from o-cresotinic acid: homohydroquinonecarboxylic acid
Hs OH CO3OH OH s OH CO 3 OH O
vom Schmelzp. 21 5 °,from melting point 21 5 °,
aus m-Kresotinsäure: Homohydrochinoncarbonsäure from m-cresotinic acid: homohydroquinonecarboxylic acid
/ I / I
vom Schmelzp. 205°.from melting point 205 °.
H C3H OH CO Oh)HC 3 H OH CO Oh)
Darstellung der Hydrochinoncarbonsäure. Representation of the hydroquinone carboxylic acid.
180 g Salicylsäure werden in 4 1 verdünnter Natronlauge (250 g Na O H enthaltend) gelöst. Unter Abkühlen giebt man · eine Lösung von 350 g Kaliumpersulfat in 3,5 1 Wasser hinzu und läfst unter Abkühlen 2 bis 3 Tage bei gewöhnlicher Temperatur stehen oder erwärmt einige Zeit auf etwa 40 °. Nachdem der active Sauerstoff verschwunden ist, was man durch Prüfen einer in der Kälte mit Salzsäure angesäuerten Probe der Lösung mit Jodkaliumstärkepapier erkennt, macht man in der Kälte sauer und schüttelt mit Aether unverändert gebliebene Salicylsäure aus. Man erhitzt sodann zum Kochen, wobei das Zwischenproduct zerfällt. Schüttelt man nun die erkaltete Lösung mit Aether aus, so erhält man als Rückstand in guter Ausbeute Hydrochinoncarbonsäure vom Schmelzp. 196 bis 1970.180 g of salicylic acid are dissolved in 4 l of dilute sodium hydroxide solution ( containing 250 g of Na OH ). A solution of 350 g of potassium persulphate in 3.5 l of water is added while cooling and the mixture is left to stand for 2 to 3 days at normal temperature while cooling or heated to about 40 ° for a while. After the active oxygen has disappeared, which can be seen by checking a sample of the solution acidified with hydrochloric acid in the cold with iodine potassium starch paper, one makes acidic in the cold and shakes out unchanged salicylic acid with ether. The mixture is then heated to a boil, the intermediate product disintegrating. If the cooled solution is shaken out with ether, hydroquinonecarboxylic acid of melting point is obtained as a residue in good yield. 196 to 197 0 .
In derselben Weise erhält man aus o- und m-Kresotinsäure Säuren, die nach ihrer Bildungsweise als Homohydrochinoncarbonsäuren aufzufassen sind. . Die aus o-Kresotinsäure erhaltene Homohydrochinoncarbonsäure schmilzt bei 215 °, die aus m - Kresotinsäure erhaltene bei 205 °. ' ,In the same way, acids are obtained from o- and m-cresotinic acid according to their mode of formation are to be understood as homohydroquinonecarboxylic acids. . The one obtained from o-cresotinic acid Homohydroquinonecarboxylic acid melts at 215 °, that obtained from m-cresotinic acid at 205 °. ',
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE81297C true DE81297C (en) |
Family
ID=353795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT81297D Active DE81297C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE81297C (en) |
-
0
- DE DENDAT81297D patent/DE81297C/de active Active
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